A cascade reaction of cinnamyl azides with vinyl sulfones directly generates dihydro-pyrrolo-pyrazole heterocycles

Angela S. Carlson; Alexandru M. Petre; Joseph J. Topczewski

doi:10.1016/j.tetlet.2021.152860

A cascade reaction of cinnamyl azides with vinyl sulfones directly generates dihydro-pyrrolo-pyrazole heterocycles

Angela S. Carlson, Alexandru M. Petre, Joseph J. Topczewski

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

2 Scopus citations

Abstract

This report describes the direct synthesis of dihydro-pyrrolo-pyrazole heterocycles from allylic azides and methyl vinyl sulfone. The product results from a complex cascade reaction that is operationally straightforward, with aromatization being the result of a concomitant elimination step. A variety of azides could participate in this reaction (12 examples) and the isolated yields of the desired product ranged from 51%−72%. Lastly the ethylene sulfone group could be removed by heating the product in pyrrolidine.

Original language	English (US)
Article number	152860
Journal	Tetrahedron Letters
Volume	67
DOIs	https://doi.org/10.1016/j.tetlet.2021.152860
State	Published - Mar 16 2021

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Publisher Copyright:
© 2021 Elsevier Ltd

Keywords

Azide
Cascade reaction
Pyrazole
Pyrrolidine
Vinyl sulfone

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title = "A cascade reaction of cinnamyl azides with vinyl sulfones directly generates dihydro-pyrrolo-pyrazole heterocycles",

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AB - This report describes the direct synthesis of dihydro-pyrrolo-pyrazole heterocycles from allylic azides and methyl vinyl sulfone. The product results from a complex cascade reaction that is operationally straightforward, with aromatization being the result of a concomitant elimination step. A variety of azides could participate in this reaction (12 examples) and the isolated yields of the desired product ranged from 51%−72%. Lastly the ethylene sulfone group could be removed by heating the product in pyrrolidine.

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KW - Vinyl sulfone

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A cascade reaction of cinnamyl azides with vinyl sulfones directly generates dihydro-pyrrolo-pyrazole heterocycles

Abstract

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